As a pythonista beginner with some (limited) python experience (MSWindows and Linux), I'd say that the biggest challenges and frustrations I've faced with Pythonista have to do with the limitations of iOS and Apple's walled garden approach, and the bizarre contortions you have to go through to overcome how hard they make it to get anything into or out of it. The other frustration is that, after you've developed something that works, you have to go through a bunch of other bizarre contortions to be allowed to let your project look and work like a real app and not have to run it from within Pythonista.
I don't see these as Pythonista problems - they're really Apple problems.
My other needs for coming up the learning curve have been met really well by asking questions here, and a lot of googling. (Not a bad way to learn, btw...) Really helpful utilities are not in the documentation. (Example: GitHubGet has been one of the most useful tools I've found, and it took me a day of poking around to find it... I kind of knew something like that HAD to exist, but it sure wasn't easy to find...)
I would love to see this stuff collected in one place, with some narrative around it to explain what problems someone is likely to run into and how to use these tools to solve them. I'd be willing to help pull something like that together, but would need to work with someone more knowledgable - I'm still feeling my way around. (Added a gui using the ui library for the first time yesterday! Before that, I wrote little hacks that were reminiscent of the programs I used to write back in the early 1980s. I've successfully moved from the early 1980s to the late 1980s!)